A fictional town can set a songwriter free. That’s the spark behind Jennyville, the creative sandbox where Jenny Tolman learned to ignore the lanes, chase characters, and write past the limits of “radio safe.” From that sandbox came a career shaped by range: the gut-punch of a military tribute that found its moment and the dance-floor joy of a Texas two-step anthem.

We go deep on Lonely In The Lone Star, co-written with Bill White and Dave Brainerd. What started as a cowboy title became a piercing story of loss through Dave’s veteran lens, written before the Afghanistan withdrawal and later embraced by grieving families. Jenny shares how a nudge to post a demo led to a memorial performance in Jackson, proceeds donated to the thirteen families, and a number-one moment powered by empathy, not hype. Then we flip the coin and step into I Know Some Cowboys, born from first tours across Texas, chivalry on the dance floor, and playful texts to Dave that turned into a sing-along hook. It’s proof that country’s heart holds sorrow and celebration with equal honesty.

We also pull back the curtain on The Road, Taylor Sheridan’s series featuring Blake Shelton, Keith Urban, and Gretchen Wilson. Jenny talks about the shock of leaving her toddler, finding real independence in empty hotel rooms, and getting a nightly masterclass side stage. The show’s commitment to authenticity over drama let the artists’ experience—and the music—take center stage. Finally, we head to Jackson Hole for Cowgirls at the Cowboy, the women-driven festival Jenny curates at the Million Dollar Cowboy Bar. With a pin-drop songwriter night, an emerging spotlight, and a headline finish, it’s a platform built to elevate stories that deserve bigger rooms.

If you love songwriting craft, real stakes, and the kind of country that builds community, you’ll feel at home here. Listen, share with a friend who needs a creative boost, and leave a quick review so more music lovers can find the show.